Ontheregioselective molecular sieves-promoted oxidative three-component synthesis of fused-benzimidazoles from β-ketoesters

MARTIN, ANTHONY; CHESHMEDZHIEVA, DIANA; PALERMO, VALERIA; LIÉBY-MULLER, FRÉDÉRIC ; ROMANELLI, GUSTAVO PABLO; GAUDEL-SIRI, ANOUK; COQUEREL, YOANN; CONSTANTIEUX, THIERRY; RODRIGUEZ, JEAN

COMPTES RENDUS CHIMIE

ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER

Lugar: Paris; Año: 2022 vol. 25 p. 19 - 29

1631-0748

The regioselectivity of molecular sieves-promoted oxidative three-component reaction between -ketoesters, aromatic o-diamines and acrolein, leading to pyrido[1,2-a]benzimidazoles, has been investigated by a combination of experimental and theoretical studies. Molecular sieves act both as heterogeneous catalyst and dehydrating agent and their role has been modeled in the theoretical approach. The modulation of the reactivity of the aromatic diamine partner as a function of the nature of the substituents of the aromatic ring and its influence on the regioselectivity of the reaction could be rationalized.